Water → HCID 67307600, compound

HRID 1260173Notes

Reaction equation

HRID 1260173 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Br:21])(=[O:3])[CH3:2].I[CH3:23].[H-].[Na+].O>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH3:23])[CH:9]=[CH:8][C:7]=1[Br:21])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67306003HCID 67306003, compound

Product 1

HCID 67307600HCID 67307600, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-(4-cyanophenylamino)benzyl acetate (1.0 g, 2.9 mmol) in N,N-dimethylformamide (11 mL) under nitrogen atmosphere was added iodomethane (0.543 mL, 8.7 mmol), and the mixture was stirred in ice-water bath for five minutes. Then sodium hydride (0.174 g, 4.35 mmol) was added, and the reaction was stirred at room temperature for 24 hours. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give crude 2-bromo-5-[N-(4-cyanophenyl)-N-methylamino]benzyl acetate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b3975c8bfa08405aa6ded5827ef44064
Source dataset
uspto-grants-2013_06
Patent number
US08470803B2

Reaction notes

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